Functionalized high cis-1,4-polybutadiene prepared using novel functionalizing agents

Abstract

In general the present invention provides a functionalized polymer prepared by a process comprising the steps of preparing a pseudo-living polymer by polymerizing conjugated monomer with a lanthanide-based catalyst, and reacting the pseudo-living polymer with a functionalizing agent defined by the formula (I) A-R 1 —Z  (I) where R 1 is a divalent bond or divalent organic group comprising from 0 to about 20 carbon atoms, A is a substituent that will undergo an addition reaction with a pseudo-living polymer, and Z is a substituent that will react or interact with silica or carbon black reinforcing fillers, with the proviso that A, R 1 , and Z are substituents that will not protonate a pseudo-living polymer.

The invention claimed is: 
     
       1. A method for preparing a functionalized polymer comprising the steps of:
 preparing a pseudo-living polymer by polymerizing conjugated diene monomer with a lanthanide-based catalyst, wherein the lanthanide-based catalyst comprises (a) a lanthanide compound, (b) an alkyl aluminoxane, and (c) a source of halogen; and 
 reacting the pseudo-living polymer with a functionalizing agent defined by the formula:
   E=C═N—R 2 —R 1 —Z  (V)
 
 
 where R 1  is a divalent bond or divalent organic group comprising from 0 to about 20 carbon atoms, R 2  is a divalent organic group, where E is O or S, and where Z is selected from the group consisting of N,N-disubstituted aminophenyl groups, cyclic amino groups, imine groups, amide groups, and epoxy groups. 
 
     
     
       2. The method of  claim 1 , where the functionalizing agent is 4-(N,N-diethylamino) phenyl-4′-isocyanatophenylmethane. 
     
     
       3. The method of  claim 1 , where E is O. 
     
     
       4. The method of  claim 1 , where E is S. 
     
     
       5. The method of  claim 1 , where R 2  is a hydrocarbylene group. 
     
     
       6. The method of  claim 1 , where Z is an N,N-disubstituted aminophenyl group. 
     
     
       7. The method of  claim 1 , where Z is a cyclic amino group. 
     
     
       8. The method of  claim 1 , where Z is an imine group. 
     
     
       9. The method of  claim 1 , where Z is an amide group. 
     
     
       10. The method of  claim 1 , where Z is an epoxy group.